Dimethylformamide → 5-Methoxy-2-methyl-1H-indole-3-carbonitrile

HRID 889901노트

반응식

HRID 889901 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2.[C:13](#[N:15])C.ClS(N=C=O)(=O)=O.CN(C)C=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:13]#[N:15]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 706425-Methoxy-2-methylindoleHCID 70918Chlorosulfonyl isocyanate

생성물 1

HCID 222500905-Methoxy-2-methyl-1H-indole-3-carbonitrile수율 67%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a 0° C. solution of 5-Methoxy-2-methyl-1H-indole (5 g, 31.0 mmol), dry acetonitrile, (90 mL) was slowly added chlorosulfonyl isocyanate (3 mL, 34.1 mmol). The reaction was stirred and allowed to warm to room temperature and stirred for an additional four hours followed by the addition of dimethyl formamide (4.8 mL (62.0 mmol)and then stirred for an additional 1.5 hours at room temperature. The reaction was poured into water and extracted with diethyl ether. The aqueous layer was adjusted to pH 9 with 1M potassium carbonate, and extracted with diethyl ether. The ether layers were combined and dried over magnesium sulfate, filtered and concentrated. Crystallization of the residue from ether and hexane gave 5-methoxy-2-methyl-1H-indole-3-carbonitrile (3.86 g) in 67% yield as a light pink solid. C11H10N2O: GC/MS r.t.=4.06 min., m/z 186; 1H NMR (CDCl3): δ 7.22 (d, 1H, J=8.3 Hz), 7.08 (s, 1H), 6.86 (d, 1H, J=8.3 Hz), 3.86 (s, 3H), 2.60 (s, 3H) ppm.

후처리

  1. customTo a 0° C.
  2. stirringstirred for an additional four hours
  3. stirringstirred for an additional 1.5 hours at room temperature
  4. extractionextracted with diethyl ether
  5. extractionextracted with diethyl ether
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customCrystallization of the residue from ether and hexane

출처 및 근거

ORD 기록
ord-ef16703b86734a708b928469a1eba742
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995171B2

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